


Lolita

by PetrichorPerfume



Series: Rainbow Marbles [96]
Category: Supernatural
Genre: Age Regression/De-Aging, Childish Sam, Crossdressing, Feminine Castiel, Feminine Sam, Feminization, Lolita, M/M, Multi, Sam-Centric
Language: English
Status: Completed
Published: 2014-07-25
Updated: 2014-07-25
Packaged: 2018-02-10 10:21:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,122
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2021379
Author URL: https://archiveofourown.org/users/PetrichorPerfume/pseuds/PetrichorPerfume
Summary: <blockquote class="userstuff">
              <p>Sam loves days like this, days when he can just shut the world away and be Sammy.</p>
            </blockquote>





	Lolita

**Author's Note:**

> Thank you to Lauren for giving me a bunch of great ideas for this.
> 
> Now for the pictures that served as part of my inspiration: 
> 
> Castiel's dress: http://www.topb2c.cc/media/catalog/product/cache/1/image/9df78eab33525d08d6e5fb8d27136e95/2/9/297d1dff-440e-417b-b3c5-59f9c301547b.jpg
> 
> Sam's outfit: http://meltydream.storenvy.com/collections/123530-pastel-galaxy
> 
> Sam's nails: http://img.over-blog-kiwi.com/0/70/32/41/20140327/ob_e0f39a_pink-galaxy-nail-art-3.jpg
> 
> Castiel's nails: http://cdn2.stylecraze.com/wp-content/uploads/2013/06/teddy-bear-nails.jpg
> 
> The bed: https://warosu.org/data/cgl/img/0075/47/1399698869045.jpg
> 
> Obviously I own none of these pictures.

Sam starts to fall the moment he wakes up to find two dressing gowns hanging from the doorway. He takes a moment just to stare at them and imagine how they feel, fingers tingling from sense memory and nose twitching as it detects just the faintest hint of vanilla in the air. He smiles approvingly. Today is a vanilla day. Days like this are always vanilla days.

 

He slowly rises from the bed and frowns a little at the cold, smooth concrete beneath his feet. Normally, it doesn’t bother him, but he’s already so much more attuned to his surroundings than he usually is that the chill feels like an affront to his senses. He pads over to the gowns and runs his hands over the skirt of his. It’s mostly white with just the barest blush of pink woven in, and it’s soft and luxurious and Sam loves the way it feels against his skin.

 

“Cas,” he whispers. It’s not loud enough to wake the former angel, but Cas wasn’t sleeping so it didn’t matter. Every time they play this game, Sam rises first and Cas pretends to be asleep to give Sam time to process the arrival of the nightgowns.

 

Cas sits up. “Yes, Sam?” He asks softly. He rises slowly and saunters over to Sam. “Would you like me to help you get dressed?”

 

Sam shakes his head. He’s not far gone enough yet to find the idea appealing, but Cas already knew that. A question like that this early on was just to remind Sam that today was for him, not Cas, not Dean, just him and him alone. He lets a sense of looseness settle across his skin like a heavy cape and gives Cas a lazy smile.

 

Cas returns it and Sam feels a little like giggling, but he doesn’t because there will be time for that later. He slips into his nightgown and watches as Cas does the same, then twirls a little bit to feel the way it swooshes against his skin. The cool silk quickly warms and Sam feels the looseness start to seep into his skin and settle inside of him.

 

When he turns around, Dean is in the doorway, smiling easily in his old-fashioned military suit with a high collar and a double row of buttons down the front. He extends one white-gloved hand and Sam whimpers, because Dean in a suit is one of his many Dean-related weaknesses. _No,_ he amends, _Dean is my weakness._

 

Dean’s smile widens and he blushes. He takes one arm and Cas takes the other and Dean wordlessly leads them down the hall into the suite they’ll be using today. The door slides shut behind them and Sam breathes a tiny sigh of relief as the outside world is closed out. Today, he’s free, in body, mind, soul, and spirit.

 

Dean settles down on the couch against the wall and pops a pipe into his mouth. He leans back on the plush pink cushions and waits for Cas to start them off.

 

“You’re looking very handsome today, Sir,” Castiel says with what Sam thinks is the prettiest blush he’s ever seen.

 

Sam matches it with a blush of his own even though the comment wasn’t directed towards him. He silently passes out the pause they always leave for him to respond so the pressure to speak right away won’t become too overwhelming for him. They don’t expect him to talk, but give him ample time to anyway because they’re both so well attuned to his needs.

 

“Thank you, Madame,” Dean says after a few moments. “I am terribly sorry that I caught you and your friend unawares before you had time to get ready for the day.”

 

Another pause. Then, “That’s perfectly okay, Sir. We’ll be ready soon.”

 

Sam lets Cas lead him to the vanity. They don’t bother with makeup because they know that Sam will just ruin it by crying later on, when he’s fallen even further. Cas smiles at him as he presses ten stickers one by one onto Sam’s nails. Sam’s breath hitches when he looks down to see the pink galaxy print nail pattern he’d chosen last time because he’s already in deep enough for something like that to matter.

 

He watches, enthralled, as Castiel quickly puts on his own nails, little pink and white polka dots with tiny bears on the ring fingers. His breath hitches because he just knows that Cas is going to look amazing, and that he’ll get to play with Cas all day and watch his polka dot bear fingers do all kinds of amazing things.

 

He lets Cas curl his hair and starts to make happy little noises at the back of his throat when he locks eyes with his reflection. Already, he looks pretty in his light pink nightgown and his curly hair and his perfectly manicured nails against the pastel colored background of the dressing room.

 

He whimpers when Cas puts on a dark blonde pigtail wig because it’s _Cas,_ and Cas is too pretty as it is. A continuous stream of little noises fall from his lips as Cas starts to tug off his nightgown, and he doesn’t even try to stop them from coming out because Cas is smiling at him and if Cas is smiling, everything must be okay, right?

 

He starts to get hard when Cas takes out a pair of billowy cotton underpants. He’s too deep for it to be sexual; right now he’s just over-excited from sensory overload. Cas strokes him a few times before tucking him away into his underwear, and he starts to cry because he’s already over-sensitive and feeling of soft cotton against his length all day is going to drive him mad. That’s the point, though; Dean likes to keep him hard and needy and desperate and strung out because he’ll be jarred out of his headspace otherwise and Dean enjoys doing this for him too much to let that happen.

 

He says something incoherent and Cas kisses along the hem of his underwear until he gets used to the sensation of being trapped within them.

 

The pastel purple socks come next and Sam coos at the tiny foxes dotted along their length. “Fox,” he giggles.

 

Cas kisses each of his knees. “Do you like foxes, Sammy?”

 

Sam nods. “We should get a pet fox.”

 

Cas laughs. “Okay, love, are you ready for your dress?”

 

Sam bites his lip. His cock throbs and he nods. He wants this, wants it so bad, and Dean and Cas are going to give it to him. He buries his face in his hands and starts to cry again.

 

Dean rises and sits down on the floor next to him. “Are you sad, sweetheart?”

 

Sam shakes his head. “’m happy,” he mumbles. “That you and Cas love me so much.”

 

Dean kisses his forehead. “Of course we love you, baby.”

 

Cas returns with the dress and Sam gasps. It’s so, so, so beautiful, and they’re going to let him wear it and play with him in it. His heart starts to pound and he mewls.

 

Dean helps him up and together, they fold him into the dress. Dean leads him to the full-body mirror and his breath catches in his throat as he takes in the purple galaxy print Lolita dress hugging his body in all the right places.

 

“You’re beautiful,” Dean whispers.

 

“Stunning,” Cas adds.

 

“Shh, I’m going to help you put on your bows while Cas puts on his dress, okay?” Dean says.

 

Sam watches as Cas puts on a green cotton candy bear print dress, a hair bow with a small plush bear on it, a cartoon bear pendant, and a pair of pastel pink socks with tiny teddies on it.

 

Dean fixes the largest bow onto the center of his dress, and two smaller bows onto his hips. He makes sure to brush his hands against his brother’s cock as often as possible until Sam is shaking and trying to thrust his hips into the delicious pressure of Dean’s hands. Dean also puts in a matching hair bow and stands back to admire his work.

 

“Gorgeous, Sammy.”

 

Sam beams at the praise. He folds his hands at his hips and starts to sway back and forth.

 

“Would you like to have a tea party, Sammy?” Cas asks.

 

Sam closes his eyes and nods. He’s always wanted to have a tea party, ever since he first learned what tea parties were. It’s a desire he’d always kept secret, and now... Now, Dean is willing to give him whatever he wants. “I’d like that,” he whispers.

 

They lead him by the hand – _like a child,_ he thinks – into another room separated from the first by a pink curtain. His heart skips a beat as he takes in the sight of the table laden with ornately decorated cakes, cupcakes, cookies, and teacups.

 

Cas pulls out a chair for him and Sam completely looses himself. He lets himself fall the rest of the way and giggles as he skips over to Cas.

 

***

 

The first time they’d done this, Sam had thought he’d feel silly wearing a dress. He thought that he’d be too big to look good in such a feminine item, but he’d been wrong. He’d taken one look in the mirror and fallen in love with the idea of wearing dresses and acting childish and girly. It made him feel free, and loved, and needed.

 

Secretly, days like there were his favorites.

 

***

 

Sam squeaks when Dean pulls him off the floor and into his lap. “I couldn’t take it anymore,” Dean confesses. “Couldn’t watch you and not touch.”

 

Sam _melts_ at the thought that Dean – calm, composed, cool, collected Dean – couldn’t wait another second to have him.

 

“You’re so fucking pretty like this, Sammy,” Dean breathes against Sam’s neck as he hitches up his brother’s skirt and frees his cock from his panties. He plays with it for a few minutes until Sam is writhing in his lap and keening from how _good_ it all is before tucking it back into his underwear, pulling down his dress, and depositing him back on the floor.

 

Sam takes a few moments to compose himself, whimpering a little at the way his cock throbs, before returning his attention to playing dolls with Cas.

 

***

 

Dean does the same thing a half an hour later. Sam starts to cry when Dean puts him down, because he’s so needy and he just wants to come but Dean won’t let him.

 

“P-please,” he hiccups.

 

Dean gently pets his hair. “But, baby, you don’t want to get your pretty dress all dirty, do you?”

 

Sam shakes his head. “N-no, Sir.”

 

Cas smiles at him and Sam forgets about everything but playing for the moment.

 

***

 

Sam snaps when Cas crawls into his lap and starts teasingly rubbing against him. He’s too sensitive and too needy and too desperate and too broken to take it, so he wraps his arms around the former angel to keep him in place and finds his release thrusting his hips against Castiel through four layers of clothes.

 

He whimpers when he’s done and starts to cry. He knows from last time that Dean won’t be harsh with him, that this is the one time he’s allowed to break the rules because Dean understands just how far he’s regressed.

 

“Come here, Sammy,” Dean says softly.

 

Sam bites his lip and blushes even though he knows that Dean isn’t mad at him. He crawls over to Dean and sits submissively at his feet.

 

Dean rubs his finger over Sam’s lips for a while to calm him down before speaking. “You made a mess of your pretty little panties, Sammy,” Dean admonishes. “What am I going to do with you?”

 

Sam sniffles. “I’m sorry.”

 

Dean leans down to kiss his forehead. “Don’t worry, sweetheart. I know you couldn’t help it. Just take them off and let Cas clean you up and all is forgiven, okay?”

 

“T-thank you,” Sam says.

 

Dean smiles down at him. “You’re so cute like this. You know that, right?”

 

Sam blushes, and once again, all is right in the world.

 

***

 

When it’s time for bed, they all snuggle up on an oversized bed with baby pink satin sheets and heart-shaped pillows. Sam lets Castiel and Dean set him down him the middle and cuddle up close on either side.

 

Cas falls asleep within fifteen minutes, but it takes Sam slightly longer. “Thanks for doing this for me, De,” he whispers sleepily. He hasn’t used that name since he was four and just learning to speak properly.

 

Dean gives him one last good night kiss. “You’re welcome, Sammy.”


End file.
